Problem: For all complex numbers $z$, let \[f(z) = \left\{
\begin{array}{cl}
z^{2}&\text{ if }z\text{ is not real}, \\
-z^2 &\text{ if }z\text{ is real}.
\end{array}
\right.\]Find $f(f(f(f(1+i))))$.
Explanation: We work from the inside out. Since $1+i$ is not real, $f(1+i)=(1+i)^2=1+2i-1=2i$. So $f(f(f(f(1+i))))=f(f(f(2i)))$. Since $2i$ is also non-real, $f(2i)=(2i)^2=-4$. So $f(f(f(2i)))=f(f(-4))$. Since $-4$ is real, $f(-4)=-(-4)^2=-16$. So $f(f(-4))=f(-16)$. Since $-16$ is real, $f(-16)=\boxed{-256}$.